Isoferulic Acid - Moligand™, ≥98% , CAS No.537-73-5

CAS: 537-73-5 Cat. No.: I131024 Formula: C₁₀H₁₀O₄ Molecular Weight: 194.18 Beilstein Registry Number: 10437 EC Number: 208-676-0

GRADE & PURITY Moligand™, ≥98%

Synonyms

DTXSID501009309 | Isoferulate | XSQ2K2G7MC | (E)-3-(3-hydroxy-4-methoxyphenyl)acrylicacid | DTXCID90908460 | Hesperetic acid | SCHEMBL249042 | 2-Propenoic acid, 3-(3-hydroxy-4-methoxyphenyl)- | 3-(3-Hydroxy-4-methoxyphenyl)acrylic acid | trans-Isoferulic

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

3-Hydroxy-4-methoxycinnamic acid is isolated from the aerial part of Artemisia capillaris, Chinese medicinal plant. It is a component of chinese herbal medicine used for a pain killer and stomachic.
3-Hydroxy-4-methoxycinnamic acid was used in the synthesis of tranilast and various tranilast analogs (cinnamoyl anthranilates) by genetically engineered Saccharomyces cerevisiae yeast strain.

Specifications

Synonyms

DTXSID501009309 | Isoferulate | XSQ2K2G7MC | (E)-3-(3-hydroxy-4-methoxyphenyl)acrylicacid | DTXCID90908460 | Hesperetic acid | SCHEMBL249042 | 2-Propenoic acid, 3-(3-hydroxy-4-methoxyphenyl)- | 3-(3-Hydroxy-4-methoxyphenyl)acrylic acid | trans-Isoferulic

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

3-Hydroxy-4-methoxycinnamic acid is bioactive metabolite of Spilanthes acmella Murr. It increases the resistance of low-density lipoprotein (LDL) to oxidation.

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Purity

≥98%

Names and Identifiers

Pubchem Sid

504760044

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504760044

Canonical Smiles

COC1=C(C=C(C=C1)C=CC(=O)O)O

IUPAC Name

(E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid

InChIKey

QURCVMIEKCOAJU-HWKANZROSA-N

INCHI

1S/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+

Isomeric SMILES

COC1=C(C=C(C=C1)/C=C/C(=O)O)O

WGK Germany

2

RTECS

UD3365400

Molecular Weight

194.18

Beilstein

10437

Reaxy-Rn

2212758

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2212758&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Cinnamic acids and derivatives
      • Subclass Hydroxycinnamic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Cinnamic acids and derivatives
• Subclass: Hydroxycinnamic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Hydroxycinnamic acids
• Alternative Parents: Coumaric acids and derivatives Cinnamic acids Methoxyphenols Styrenes Phenoxy compounds Methoxybenzenes Anisoles Alkyl aryl ethers 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Cinnamic acid - Coumaric acid or derivatives - Hydroxycinnamic acid - Methoxyphenol - Phenoxy compound - Anisole - Methoxybenzene - Styrene - Phenol ether - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Phenol - Monocyclic benzene moiety - Benzenoid - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Ether - Organic oxygen compound - Carbonyl group - Organic oxide - Organooxygen compound - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as hydroxycinnamic acids. These are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
• External Descriptors: ferulic acids

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

PMVK Tchem Phosphomevalonate kinase (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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TYR Tclin Tyrosinase (717 Activities)

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HT-1080 (3966 Activities)

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A549 (127892 Activities)

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HeLa (62764 Activities)

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HYAL1 Tbio Hyaluronidase-1 (8 Activities)

Discover Target: HYAL1

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GNAS Tbio Guanine nucleotide-binding protein G(s), subunit alpha (103405 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

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CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

Discover Target: CBX1

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Associated Targets(non-human)

Ralstonia solanacearum (520 Activities)

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Trypanosoma brucei brucei (13300 Activities)

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RAW264.7 (28094 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Melt Point(°C): 230°C
• Molecular Weight: 194.180 g/mol
• XLogP3: 1.500
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 194.058 Da
• Monoisotopic Mass: 194.058 Da
• Topological Polar Surface Area: 66.800 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 224.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1